Michael Saylor’s company just made another massive bet on Bitcoin—and it’s one of the biggest purchases of the year.

The company just dropped a huge amount of cash on Bitcoin - we're talking $1.28 billion. This big purchase brought their total Bitcoin holdings to around 738,750 BTC. And with the price of Bitcoin hovering around $68,500, their crypto stash is now valued at a whopping $50.5 billion.

This purchase is a big deal for Saylor - it's not just any ordinary buy. He's actually calling it the start of his company's "second century", and that's because they've just made their 100th Bitcoin acquisition. This is a major milestone, especially since they only started this strategy back in 2020.

A New Funding Engine for Buying Bitcoin

To pay for the purchase, Strategy relied a lot on a special kind of financial tool called STRC, which is a type of preferred share that has a variable interest rate.

The company just raised a huge amount of money - $377 million - by issuing STRC. And the best part is, STRC is currently paying out a dividend of around 11.5% per year, which works out to monthly payments.

At the same time, the company sold almost $900 million of its own stock, and they used this money along with other funds to keep buying more Bitcoin aggressively.

STRC is set up to trade at around $100 per share. If the price goes above that, the plan is to release more shares and use the money to buy more Bitcoin. This way, the price should stay close to $100. The idea is to keep the price stable by balancing the number of shares with the amount of Bitcoin owned.

The company has so far handed out around $3.8 billion in STRC, and this is since they first brought out the product.

One of the Largest Purchases This Year

This recent purchase is Strategy's second-biggest Bitcoin investment so far in 2026.

The company made a big purchase in January, buying a lot of 22,300 BTC. This happened after they got a lot of money - $294 million from STRC and $1.8 billion from common stock offerings.

After buying more Bitcoin, Strategy's average cost per Bitcoin is about $75,800. This means they're currently holding a loss of around $5.5 billion that hasn't been realized yet.

In total, Strategy has invested a whopping $56 billion in Bitcoin over time.

Investors Remain Divided

Despite the bold strategy, the company’s stock has faced volatility.

The company's stock has gone up a bit, by about 2.8%, to $137. This is a small recovery from last month when it was really low, near $104. But overall, the stock is still down a lot, about 58%, over the past six months.

Some analysts say Strategy’s decision to build cash reserves earlier helped prepare for this aggressive expansion. Others worry that issuing dividend-paying shares like STRC adds long-term financial pressure.

Still, Saylor appears unfazed.

He's still got his eyes on the prize: keep buying up Bitcoin and make the company the biggest player in the game, with the most Bitcoin holdings of any corporation.

If the market eventually takes a turn for the better and becomes bullish once more, that huge bet could end up being what defines Strategy's future path.

Strategy Drops $1.28 Billion on Bitcoin, Issues $377 Million in Preferred Shares

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